Grayson Square Homes with Gated Amenities

Welcome to Grayson Square, an exquisite subdivision nestled in the heart of Winter Park, Florida, within the charming Seminole County. This vibrant community is perfect for those seeking a blend of luxury, comfort, and security. Grayson Square boasts beautifully designed homes that cater to a variety of lifestyles, making it an ideal choice for families, professionals, and retirees alike.

One of the standout features of Grayson Square is its gated amenities, providing residents with peace of mind and a sense of exclusivity. The meticulously maintained entrance ensures that you and your loved ones can enjoy the serene surroundings without the worries of outside disturbances. As you explore the neighborhood, you'll discover a range of modern homes, each showcasing unique architectural styles and high-end finishes that reflect the sophistication of Winter Park living.

Beyond the gates, the community offers a plethora of recreational options, including picturesque walking trails, lush green spaces, and nearby parks perfect for family outings or leisurely strolls. The vibrant downtown area of Winter Park is just a short drive away, where you can indulge in boutique shopping, delightful dining experiences, and cultural attractions such as art galleries and museums.

Grayson Square is not just a place to live; it's a lifestyle. With its prime location, luxurious homes, and gated amenities, this subdivision is the perfect sanctuary for those looking to embrace the best of Florida living. Come and discover the charm and elegance of Grayson Square—your dream home awaits!

Newest Grayson Square Homes with Gated Amenities

$409,900

3 Beds ⋅ 3 Baths ⋅ Grayson Square SubDv. ⋅ 32792 Zip Code

Almost brand new and move in ready CORNER townhome in Winter Park! This beautiful 3 bedroom 2.5 bathroom home with just under 1,800 sq. ft. offers a large 2 car garage, light and bright living spaces, clean and modern designer features, and comes equipped with a full kitchen appliance package and washer/dryer. The first floor offers expansive living spaces with enough room for a dining area and family room. All of which flow seamlessly into the open kitchen. With white cabinets and Quartz counter tops, the kitchen is a show stopper! The entire first level is adorned with tile and offers a half bathroom and access to the covered back porch. Just up the stairs, you will find all of your bedrooms and full bathrooms. The primary bedroom and en suite bathroom are ample in size and also offer a large walk in closet. Both secondary bedrooms are down the hall and share a large full bathroom. The small gated community of townhomes offers a community pool and serene pond. HOA includes cable! Make sure to put this on your must see list!

2857 Clever Lane, Winter Park

$389,900

3 Beds ⋅ 3 Baths ⋅ Grayson Square SubDv. ⋅ 32792 Zip Code

BUYER INCENTIVE! Nearly-New 2023 Pulte Townhome • 3BD/2.5BA + Garage • Quartz Counters • Rate Buydown Available Imagine owning a beautifully maintained, nearly-new Pulte townhome in the heart of Winter Park. Built in 2023 and still covered by the transferable Pulte 10-year structural warranty, this home offers modern design, energy efficiency, and peace of mind. The seller is offering a rate buydown incentive toward allowable closing costs or prepaid expenses with an acceptable offer—making this one of the most affordable opportunities in the community. Located in the gated community of Grayson Square, this stylish two-story residence features an attached one-car garage and an open-concept main living area perfect for entertaining. The kitchen showcases elegant Quartz countertops, Whirlpool stainless steel appliances, ample cabinetry, and a large island overlooking the living and dining spaces. Washer and dryer are included for added convenience. Enjoy upgraded smart-home technology and fiber-optic high-speed internet and cable, already included in the low HOA—ideal for working from home or seamless streaming. Upstairs, the spacious primary suite offers a generous walk-in closet and a private en-suite bath designed for comfort and relaxation. Two additional bedrooms provide flexible space for family, guests, or a dedicated home office. With no direct rear neighbors, the covered back patio offers peaceful outdoor views. The community is beautifully maintained and features a resort-style pool, cabana, and sidewalks perfect for evening strolls. Grayson Square also maintains escrow reserves for future roof replacement and exterior painting, adding to the low-maintenance lifestyle. This prime Winter Park location places you minutes from shopping, dining, gyms, entertainment, parks, and three local colleges, as well as top commuter routes like 417—giving you easy access to everything Central Florida has to offer while coming home to a quiet, friendly neighborhood. If you’re looking for a modern, energy-efficient home with premium finishes and virtually maintenance-free living, this is the one you’ve been waiting for

2017 Canny Cove, Winter Park

Start Your Search